Visible-light-mediated synthesis of oxime esters via multicomponent reactions of aldehydes, aryl amines, and N-hydroxyphthalimide esters

Oxime esters are useful scaffolds in many organic chemistry transformations. Herein, a novel visible-light-mediated three-component reaction for synthesis of oxime esters is reported. Aldehydes, aniline, and N-hydroxyphthalimide (NHPI) esters were used as substrates in this three-component reaction, and eosin Y was used as a crucial photocatalyst for the reaction. Wide ranges of aldehydes and NHPI esters were well tolerated in this reaction method, generating various oxime esters with high efficiency under mild reaction conditions. This visible-light-mediated methodology will be a promising approach to synthesize useful oxime esters in a single step.


Table of Contents
Table of Contents

General Information
Commercial chemicals and solvents were used without any purification.Reaction progress was analyzed by thin-layer chromatography (TLC) using silica gel 60 F 254 pre-coated aluminum plate from Merck and TLC spots were observed under UV light (254nm) exposure.
Flash chromatography was carried out using 230-400 mesh silica gel and analytical grade solvents.Stuart SMP10 Melting Point Apparatus was used to record melting points of products.Structure elucidation by NMR ( 1 H and 13 C NMR) was performed on Bruker Avance 400 MHz spectrometer.The chemical shifts were reported in δ units (ppm) relative to the residual protonated solvent resonance, the coupling constants (J) quoted in Hz, and multiplicity of signals was abbreviated as follows: singlet (s); doublet (d); doublet of doublet (dd); triplet (t); multiplet (m).

Screening of reaction conditions for the synthesis of oxime esters
Table S1.Screening of reaction condition in the synthesis of oxime esters a

Table S2 .
Amount of eosin Y in the preparation of oxime esters.